I for one am glad this question came up and is being answered by very knowledgable people. I have been in the market for a 993 or 996 and could not quit decide between them.I've owned a few p cars before ( 928's) I'm definantly sold on the 993 now.

 

Using it as intended.

 

I have had both. I bought a 996tt/X50 in August. Near perfect in every way...fast, comfotable, great to look at (arctic silver over blk). I sold it less than three months later. Why? I did not bond with it like I did my 911 SC or my Cayman S. I went for a test drive in a 993 and instantly FELL IN LOVE! I am 49 and like the look, feel and smell of old school. I do I pods, but still love to pull out my vinyl.

I bought a 96 993 last month (less than a week after selling my 996!) and am so happy. That said, the guy who bought my 996tt is an air force guy who seemed to fit in that car like he would fit into a fighter jet...So, it depends...ask yourself what other things you like in life...old school or hi tech comfort. Then, extrapolate!
btw, reliability and cost? I have not had to do any thing to either (in a total of 3 1/2 months of ownership...total!!) but suffice it to say good examples are reliable but are expensive to fix and upgrade no matter what. 996's I understand are as reliable as any modern car...and just as, uhm, exciting. (sorry, couldnt resist!)

 

I've owned both too. Traded my 996/X51 for a 993C2S.

I preferred the interior of the 996/X51 and the exterior of the 993C2S.

The 993 is great and old school, but it's showing it's age (more chips, worn leather seats, ancient dash board). I find the 996 cheaper to maintain than the 993 mainly because it's a newer car.

Although they're both 911s, they feel very different. The 996 feels more refined and different gear ratio (found my self in 5th and 6th gear more often). The 993 feels more old school (rarely in 6th gear...most often in 4th gear). In my opinion, the 997 combined the best of the 996 and 993.

My shallow opinion...it's all about the bootie . Get the biggest bootie you can afford.

 

I thought the interior of the 996 was cheaper and not as attractive...the way the intrument cluster hood is plopped on top of the dashboard for instance...instead of one peice. Even thought the ergonomics of the 993 are strange, I like the simplicity of of the dials. Thankfully, I have no wear and tear yet.

On another note, can you post a picture of the dragonfly green car? I am curious about all the Porsche greens!
Enjoy!